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A three dimensional framework induced by π···π stacking of 2,2′-(Alkylene-1,6-diyl)diisoquinolinium from Q[6]-based Pseudorotaxane

  • Zhi-Fang Fan
  • Xin Xiao
  • Yun-Qian Zhang
  • Sai-Feng Xue
  • Qian-Jiang Zhu
  • Zhu Tao
  • Gang Wei
Original Article

Abstract

A bromide salt of 2,2′-(hexane-1,6-diyl) diisoquinolinium (K6) was designed, synthesized and introduced to construct a novel framework induced by π···π stacking of 2,2′-(alkylene-1,ω-diyl)diisoquinolinium from Q[6]-based pseudo-rotaxanes. The crystal structure of the compound revealed that the assembled framework based on the Q[6]-2,2′-(alkylene-1,6-diyl)diisoquinolinium pseudo-rotaxanes have stoichiometries of {(K6)@(Q[6])}2+·2Br·7(H2O). The compound 1 has a novel three-dimensional framework constructed of two different channels―one containing stacked isoquinolyl moieties from the K6@Q[6] pseudorotaxanes and the other containing the bromide anions. 1H NMR spectra analysis was performed and confirmed the pseudorotaxane interaction model in which the 2,2′-(alkylene-1,6-diyl)diisoquinolinium guest threads into the cavity of Q[6] with the alkyl chain included inside the cavity and the two end isoquinolyl moieties protruding from the two opening portals. Absorption spectrophotometric and fluorescence spectroscopic analyses of the host–guest inclusion complex in aqueous solution found that the complexes were most stable at a host:guest mole ratio of 1:1. At this ratio, the complex has binding constants (K) ~106.

Keywords

Isoquinolinum derivatives Cucurbit[6]uril Pseudorotaxanes π···π stacking Framework 

Notes

Acknowledgments

This work was supported by the National Natural Science Foundation of China (NSFC; No. 20961002), the “Chun-Hui” Fund of the Chinese Ministry of Education, the Science and Technology Fund of Guizhou Province and the International Collaborative Project Fund of Guizhou province. All are gratefully acknowledged.

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Copyright information

© Springer Science+Business Media B.V. 2011

Authors and Affiliations

  1. 1.Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou ProvinceGuizhou UniversityGuiyangPeople’s Republic of China
  2. 2.Liupanshui Normal CollegeLiupanshuiPeople’s Republic of China
  3. 3.CSIRO Materials Science and EngineeringLindfieldAustralia

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